Method for preparing 4,4′-dihydroxy-[1,1′-biphenyl-3,3′-dicarboxylic acid]

Patent metadata

Field	Value
Publication number	US-11465959-B2
Application number	US-201917050925-A
Country	US
Kind code	B2
Filing date	Apr 30, 2019
Priority date	Apr 30, 2018
Publication date	Oct 11, 2022
Grant date	Oct 11, 2022

Abstract

The present invention relates to a method for preparing 4,4′-dihydroxy-[1,1′-biphenyl-3,3′-dicarboxylic acid], the method comprising a step for preparing a compound represented by chemical formula 1 by reacting a compound represented by chemical formula 2 with a base according to reaction formula 1. [reaction formula 1] [chemical formula 1] [chemical formula 2] According to the present invention, because use of additional carbon dioxide is unnecessary during the reaction, internal pressure is lowered during same, the reaction can be carried out at a lower temperature, the yield from the synthesis is notably improved as hardening of the resulting substance is absent, and H4dobpdc can be synthesized in large amounts as an additional process for obtaining pure ligands is unnecessary.

First claim

The invention claimed is:

1. A method for preparing 4,4′-dihydroxy-[1,1′-biphenyl-3,3′-dicarboxylic acid] represented by Formula 1, comprising reacting the compound represented by Formula 2 with a base, as depicted in Reaction 1:

wherein Reaction 1 is carried out in a solvent represented by Formula 3:

wherein R 1 is H or —(CH 2 ) n —CH 3 , R 2 is —(CH 2 ) m —CH 3 , R 3 is —(CH 2 ) p —CH 3 , and n, m, and p are each independently an integer from 0 to 20,
wherein the base is selected from the group consisting of K 2 CO 3 , Na 2 CO 3 , and Li 2 CO 3 .

2. The method according to claim 1 , wherein the solvent represented by Formula 3 is selected from the group consisting of the compounds represented by Formulae 4 to 7:

3. The method according to claim 1 , wherein the base is used in an amount of 2 to 4 equivalents per equivalent of the compound represented by Formula 2.

4. The method according to claim 1 , wherein the solvent represented by Formula 3 is used in an amount of 1 to 30 equivalents per equivalent of the compound represented by Formula 2.

5. The method according to claim 1 , wherein Reaction 1 is carried out at a temperature of 170 to 230° C.

6. The method according to claim 1 , wherein Reaction 1 is carried out for at least 12 hours.

Assignees

• Univ Korea Res & Bus Found

Inventors

• Hong Chang Seop
• Choe Jong Hyeak
• Kim Jeong Eun

Classifications

• C07C51/15 Primary

  by reaction of organic compounds with carbon dioxide, e.g. Kolbe-Schmitt synthesis · CPC title

• C07C51/50

  Use of additives, e.g. for stabilisation · CPC title

• C07C65/105

  polycyclic · CPC title